real estate investing | Couple Wealth
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Some people don’t want to spend their entire life working for someone else. Shadow Skaggs is one of them and he has built multiple businesses to allow him financial freedom.

Shadow has built an impressive portfolio of real estate, started a home care agency, and invests in other opportunities. In a few short years, he has shifted from working as a full-time nurse to an entrepreneur.

Working a 9 to 5 job can provide stable income but limits your true income potential. Instead of working for someone else, the most successful people know that they should work for themselves.

We took a look at how Shadow Skaggs has built multiple profitable income streams and quit his full-time job.

Quick Look: Shadow Skaggs

Shadow Skaggs has successfully built a wide range of income streams that has allowed him to escape the 9 to 5 grind. His experience includes:

  • Real estate investment portfolio of over $1 million
  • Home care agency franchise owner
  • House flipping
  • Dividend investing
  • Flipping video games
  • Local news and media company
  • Serial entrepreneur

Let’s take a closer look at how this 33-year-old has built these businesses. You can follow his journey on Twitter @ShadowSkaggs.

Starting Out in a Nursing Career

Like many people, Shadow went to college and got a degree. He earned his Bachelor of Science in Nursing, or BSN, and spent the first several years of his career as a Registered Nurse.

This is the type of career advice many people get from their family. Go to school get a degree, and get a job that pays well. That is the exact formula that my parents preached to me and I followed, getting a degree in engineering.

Now, this is not bad advice to follow, but it is not always the best path for everyone. Shadow read “Rich Dad Poor Dad” while in college and it changed his way of thinking completely.

Instead of working for someone else for a set salary, he realized he wanted to make money work for him. Working a traditional nursing job for the rest of his life just didn’t seem appealing to him.

This got him started looking for opportunities to build his own business and start working for himself.

Shadow used his nursing skills to earn a stable income for the first few years of his professional career. During that time, he worked to find and launch his first businesses that would allow him to become an entrepreneur.

Building a Home Care Agency

A natural progression for Shadow was to start a home care business using his nursing skills. As his main business right now, Shadow provides caregivers to seniors who need help in their daily life. They help seniors with their activities of daily living, meal prep, and housekeeping.

He is a franchise owner at FirstLight Home Care, which helped to get his business up and running quickly. Through a lot of hard work, they grossed over a million dollars in sales last year and it was only the 3rd year in operation.

This is a great example of how to move from working for a boss to working for yourself. By building his own business, Shadow was able to quit a high-paying nursing job and become his own boss.

However, he didn’t stop with just one source of income in his home care agency. He also has built a real estate portfolio and invests in the stock market to continue to grow his wealth.

Moving into Real Estate Investing

Besides home care, Shadow has also built a portfolio of 22 real estate properties over the past few years. They each serve to bring in consistent rent payments and should appreciate over time, helping to generate wealth.

Once he realized he wanted to get into real estate, Shadow sought out an informal mentor to help him get on the right path. He knew a local real estate agent that also had rental properties, so he asked for his advice.

Shadow kept bringing properties that he thought would be a good investment to his mentor but would get shot down each time. After 2 years, he finally found a property that his mentor agreed would be a good first investment.

It was three single-family homes in one deal for $130,000 on a land contract. Since it was owner financed, Shadow didn’t need to use a bank and was able to get started with less than $10,000 down. He did use a lawyer to make sure all the paperwork was in order to protect himself.

For a new real estate investor, this was an ideal scenario. He needed minimal money down and there was less risk by going with a multi-family property.

The best part? It has turned out to be a solid investment over the years. The three units bring in around $1,550 per month in rent, of which $620 goes to the previous owner. Even after all other expenses, this one deal brings in around $500 per month.

Scaling Up with Real Estate

Over the past 5 years, Shadow Skaggs has continued to grow his portfolio to 22 different properties. It is mostly single family homes but he also has a couple of duplexes and a 5-unit property. He also has a commercial unit to provide some diversification.

Reinvesting his cash flow in new properties has allowed him to continue to expand his portfolio. Shadow has also taken advantage of strategically selling at the right time to make a profit.

For example, he had the opportunity to sell 3 units at once for a 40% profit. By doing that deal, he will be able to make more cash that will allow him to buy 4 or 5 new units. He has also flipped two different properties to help generate quick cash.

This year, he is planning to continue to buy more multi-family units because they are easier to maintain and have less risk. He also owns 5 acres of land that he would like to develop into a community with smaller houses.

His last goal for this year is to purchase a vacation home that his family can use for a few weeks out of the year. For the rest of the year, he can rent it out to cover the cost of the property and generate passive income.

Tips for Real Estate Investing in Rural America

Shadow has found success in investing in real estate in rural America and, more specifically, Kentucky. Here are some of his tips for finding the right investment property.

  • Never buy a house that won’t rent for 1% of the purchase price monthly. Make sure the cash flow after expenses make the investment worth your time.
  • Never buy a house below the road. The recent flooding in many areas of the country serves as a great reminder for this rule.
  • Look at the overall quality of the structure and condition before buying.
  • Make sure it is in a good location to attract dependable renters.
  • The price has to be right. Look for deals that will let you minimize the amount of cash you need upfront.

When asked for his advice on getting started, Shadow says to “just get started. I’ve seen so many people not take the first step because of fear that their plan isn’t perfect. It will never be perfect. Just get going on something.”

He also says that it is okay to have a traditional 9 to 5 job while you are scaling a side hustle. Building a side hustle takes time and it doesn’t mean that you are a failure if you don’t see profits right away. Be patient and keep working towards your goals.

Shadow Skaggs is a father, Kentuckian, real estate investor, entrepreneur, house flipper, dividend investor, and side hustler. He is the owner of Maple Hill Properties, LLC., FirstLight Home Care, Ravenwood Enterprises, LLC., and Carter County Post. You can follow him on Twitter @ShadowSkaggs and find out more at

Key Takeaways

  • Don’t settle for having to work a traditional job for the rest of your life.
  • Build multiple income streams that will allow you financial freedom. Diversify your income across different types of businesses and investments.
  • Use your skills and professional knowledge to create your own business or passive income.
  • Minimize the risk of real estate investments by choosing properties that can be rented for at least 1% monthly and have high potential to attract renters.
  • As you make money, roll that cash to new investments that will allow you to grow your overall portfolio.

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